Trifluoromethyl phenyl-beta-naphthylamines



Eatented Oct. 23, 1951 UNITED STATES PATENT OFFICE TRIFLUOROMETHYL PHENYL-fl NAPHTHYLAMINES Nathan L. Smith, Indian Head, Md.

N 0 Drawing. Application October 30, 1950, Serial No. 193,014

2 Claims.

(Granted under the act of March 3, 1883, as amended April 30, 1928; 370 O. G. 757) This invention relates to new compounds, more particularly to new phenyl-fi-naphthylamine derivatives containing a trifluoromethyl group.

The new compounds of the invention are trifluoromethyl phenyl-fl-naphthylamines which correspond to the general formula:

ere

wherein R is hydrogen or the trifluoromethyl radical.

The new compounds have antioxidant activity for gasolines and petroleum oils and for synthetic lubricants such as diesters and polyethylene glycol. Due to the presence of the trifluoromethyl group in the molecule the compounds have enhanced solubilities in hydrocarbons.

The new compounds can be prepared by condensing p-naphthol or the trifluoromethyl substituted- S-naphthol, e. g., 8-trifluoromethyl-flnaphthol with the corresponding trifluoromethyl aniline, e. g., 3-trifluoromethyl aniline, in the presence of iodine as a catalyst for the condensation.

The preparation of the new compounds is illustrated by the following specific example in which parts are by weight:

Example A mixture of 72 parts (0.5 mol) p-naphthol and 80.5 parts (0.5 mol) B-trifluoromethyl aniline is heated under reflux for 24 hours in the presence of 0.5 part iodine. The resulting dark oil is taken up in toluene, washed by shaking with dilute (about 10%) aqueous sodium hydroxide, and dried over sodium sulfate. After removing the mg tgk wherein R is a radical selected from the group consisting of hydrogen and the trifluoromethyl radical.

2. As a new compound, 3-(trifluoromethyl) phenyl-fi-naphthylamine.

NATHAN L. SMITH.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,212,825 Daudt et a1. Aug. 27, 1940 2,432,393 Dickey et al Dec. 9, 1947 OTHER REFERENCES Swarts, Beilstein (Handbuch, 4th ed.) vol. 12, p. 870 (1929). 

1. A TRIFLUOROMETHYL PHENYL-B-NAPHTHYLAMINE OF THE GENERAL FORMULA: 